☆ 4.5 Article

Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Indolylnitroalkenes

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2012)

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

卷 2012, 期 6, 页码 1230-1236

出版社

WILEY-V C H VERLAG GMBH

DOI: 10.1002/ejoc.201101648

关键词

Synthetic methods; Asymmetric synthesis; Homogeneous catalysis; Rhodium; Heterocycles

类别

Chemistry, Organic

资金

National Natural Science Foundation of China (NSFC) [21072186, 20872139]
West Light Foundation of CAS
National Basic Research Program of China (973 Program) [2010CB833300]
Chengdu Institute of Biology, CAS [Y0B1051100]

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Protocol

Reagent

摘要

Indolylnitroethanes and their derivatives are key intermediates to many bioactive structures. Most approaches to access chiral indolylnitroethanes involve organocatalyzed or metal-catalyzed asymmetric FriedelCrafts reaction of indoles with nitroalkenes. We have developed an efficient approach to optically pure a-aryl-3-indolylnitroethanes through rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to indolylnitroalkenes. Excellent yields (up to 99?%) and enantiomeric excesses (up to 99?% ee) of chiral indolylnitroethanes were achieved under mild conditions.

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